Sarah Biren
Sarah Biren
April 20, 2024 ·  6 min read

I’ve slept in cardboard boxes, vans and trucks. Now I live with my three dogs in a 25-foot sailboat

Tate Hill has lived a unique life. He’s resided in vans, cars, and boats over the past two decades, as he travels across Canada, doing odd jobs to make ends meet. He currently lives in a sailboat house, and his main companions are three dogs. His life changes frequently, but the one thing that has remained consistent is his kindness and optimism. 

However, when Hill couldn’t pay for his 25-foot boat to dock at the marina for the winter, a group of neighbors came together to help their friend. Their goal of $2,000 turned into over $17,000.

This is Tate Hill’s amazing story.  

Tate Hill, His Sailboat House, and His Three Dogs 

“I was raised in foster care in Toronto, and I’ve been fending for myself ever since,” Hill tells Dave Zarumfrom Toronto Life.  

As a child, Hill suffered from epilepsy and experienced frequent seizures. This issue still affects him today. He specifies that the seizures sometimes cause him to forget certain things. “But sometimes forgetting things makes it easier to get through life.” [1] 

Hill has wandered across Canada, living in whatever vehicle he had at the moment, from trucks to camper vans to an old Dodge Caravan. He drove, picked up odd jobs to pay for food and fuel, and would drive on. 

Dogs have always been his closest companions. They are the friends who accompany him across his travels. 

Image Credit: Toronto Life

“My first dog was a rottweiler named Angel. Once, my car broke down near Medicine Hat, and some guys helped me with my car and let me and Angel stay at their place. One of them told me, ‘If you’re going to Fort Mac, one dog isn’t enough to protect you.’ So I got more dogs.” 

He currently cares for three dogs. First, there’s Holly, who he nicknamed ‘Holly Jolly’ since he got her around Christmas time last year. Then there’s Patches who Hill got on his birthday five years ago. And Hill rescued Prince from Kijiji seven years ago. Together, they create a tight bond. “They’re the most important part in my life, and I take pride in caring for them.”  

Living in a Sailboat House off Shores of Toronto 

However, Hill suffered after a bad fall and began to live on disability. He used the money to buy a 14-foot sailboat house when he returned to Toronto. His dream is to sail across the ocean, so he’s slowly upsizing until he gets a boat capable of making the voyage.  

“I just want to go places and help people,” he explains. “My dream is to have enough money to sail south, where hurricanes have destroyed homes, and to help rebuild them in exchange for food. I want to continue to see this world, see the good things we have, and help as many people as I can.” 

His next boat was a Matilda 20 sailboat, but this new vessel didn’t last. When Hill lost the keel while sailing a week later, he sold it for $1,200. Two years ago, Hill acquired the boat he lives in now, a 25-foot sailboat house that cost $2,000. He named it Little Dog Darn Boat and painted the chipped hull to a bright red. 

This boat has become Hill and his dog’s home. Hill keeps it anchored in Humber Bay. Every day, they ride to shore on a little motorized dinghy where Hill takes them for a walk. “The dogs are good sailors. They know how to move when the boat is rocking.

“The way I see it, every time we get out on the water it’s practice for when the four of us set sail on our adventure around the world.” 

“At the end of the day, I’m happy to come back home…”

Hill dislikes relying on others, and he’s not one to beg for charity either. However, being on disability, he barely has enough to feed himself and his dogs. “Some days, I go to Lakeshore and Windermere, where I try to make people smile in exchange for money… I hold funny signs… I used to hold a sign that said ‘I’m single, 416-XOX-XOXO’.” (416 is the main area code in Toronto.)

Despite living in conditions that other people would balk at, Hill is content with his lot. His boat is much better than the other places he had to live. “At the end of the day, I’m happy to come back home. It’s just a gorgeous, beautiful boat. I’ve slept in bushes in minus-40-degree weather. I’ve slept on cardboard boxes and in vans. The water is 100 times better than the road. I feel so much safer in my boat. The dogs and I keep each other warm.” 

He’s truly made the place his home with some decorations, a small heater, and an old laptop where he occasionally watched DVDs.  

The neighbors noticed the little red boar in the harbor. “It’s like a kid’s book — the little red sailboat in the bay, it is always there,” says resident Evan Clifford. “No one really knew who he was.” 

A Change for the Better 

“Recently, I met some new friends, and everything changed for me,” Hill says.  

Fellow sailor Clifford met up with Hill. He said, “Tate, sailors look out for sailors.” 

He posted Hill’s story on Facebook and people jumped forward to donate food and supplies. Hill’s new friend, Melanie, set up a GoFundMe page. The money has raised enough money for Hill to dock his boat at the marina and take care of the hounds. “It’s completely changed my life.” Not only that, he got offered a job at a funeral parlor. 

red sailboat humber bay toronto
Image Credit: Blog TO

Now that people know the man behind the iconic boat, they are inspired by Hill. “People look out their window in the morning and there is the little red sailboat and now that they know the story of it, people are associating that little red sailboat with hope and courage,” says Clifford. [2] 

“I don’t want to rely on the kindness of others,” Hill says. “…But I’m so grateful for these new friends and their generosity. I’m going to look for every chance I get to pay it forward.  

“To be honest, I’ve never felt what I’m feeling right now. The other night, my chest and arms were shaking. I called Evan. ‘I don’t know what this is,’ I said. ‘Are you sure you’re not freezing cold?’ Evan asked me. I told him, ‘No, I think this is happiness.’” 

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  1. [1] Dave Zarum. “I’ve slept in cardboard boxes, vans and trucks. Now I live with my three dogs in a 25-foot sailboat in Humber Bay.” Toronto Life. December 11, 2020 
  2. [2] Karen Longwell. “People in Toronto raise money to give man living on sailboat a place to dock for winter.” Blog To. December 1, 2020